The Connecticut River Valley was first inhabited by Englishmen in 1633 — a post was established at Windsor, Connecticut by traders from the Plymouth Plantation. In 1636, Massachusetts Bay Colony assistant treasurer and Puritan iconoclast William Pynchon led a group of settlers from Roxbury, Massachusetts to establish Springfield on land that scouts had vetted the previous year. They considered it the most advantageous land in the Connecticut River Valley for farming and trading. This settlement, on fertile farmland just north of the Connecticut River's first major falls (at Enfield Falls), the place where seagoing vessels necessarily had to transfer their cargo into smaller shallops to continue northward on the Connecticut River, quickly became a successful settlement — largely due to its advantageous position on the Bay Path to Boston, the Massachusetts Path to Albany, and beside the Connecticut River. Originally, Springfield spanned both sides of the Connecticut River; the region was eventually partitioned. The land on the western bank of the Connecticut River became West Springfield, Massachusetts. West Springfield's northernmost parish (alternately called Third Parish, North Parish, or Ireland Parish) became Holyoke, named after earlier Springfield settler William Pynchon's son-in-law, Elizur Holyoke, who had first explored the area in the 1650s.[2] The village of Holyoke was first settled in 1745 and was officially incorporated in 1850.

The first post office in the area was called Ireland. It was established June 3, 1822, with Martin Chapin as first postmaster. It was discontinued in 1883. Another post office called Ireland Depot was established February 26, 1847, with John M. Chapin as first postmaster and had its name changed to Holyoke (with George Whittle as first postmaster) March 14, 1850.[3]

A part of Northampton known as Smith's Ferry was separated from the rest of the town by the creation of Easthampton in 1809. The shortest path to downtown Northampton was on a road near the Connecticut River oxbow, which was subject to frequent flooding. The neighborhood became the northern part of Holyoke in 1909.[4]

Holyoke had few inhabitants until the construction of a dam and the Holyoke Canal System in 1849 and the subsequent construction of water-powered mills, particularly paper mills. At one point over 25 paper mills were in operation in the city; the population rose from just under 5,000 in 1860 to over 60,000 in 1920. In 1888, Holyoke's paper industry spurred the foundation of the American Pad & Paper Company, which as of 2007[update] is one of the largest suppliers of office products in the world. The availability of water power enabled Holyoke to support its own electric utility company and maintain it independently of America's major regional electric companies. The city was thus a rare unaffected area in the Northeast blackout of 1965, for example.

Holyoke was one of the first planned industrial communities in the United States. Holyoke features rectilinear street grids — a novelty in New England. This street hierarchy is seen as a potential economic development tool as it lends well to high-rise buildings, and the surrounding canals could be landscaped into a source of recreation and relaxation. Its grid pattern is notable in Western Massachusetts, where few roads are straight. The city's advantageous location on the Connecticut River — the largest river in New England — beside Hadley Falls, the river's steepest drop (60 feet), attracted the Boston Associates, who had successfully developed Lowell, Massachusetts' textile industry.[5] From the late 19th century until the mid-20th century, Holyoke was the world's biggest paper manufacturer.[5] The elaborate Holyoke Canal System, built to power paper and textile mills, distinguishes it from other Connecticut River cities. Holyoke is nicknamed 'The Paper City' due to its fame as the world's greatest paper producer.

As of the census of 2010, there were 39,878 people, 14,977 households, and 9,478 families residing in Holyoke. The population density was 1,871.8 people per square mile (722.5/km²). There were 16,229 housing units at an average density of 762.5 per square mile (294.0/km²). The racial makeup was 61.76% White (Non-Hispanic White 47.1%), 5.8% African American (Non Hispanic 3.4%), 0.38% Native American, 1.81% Asian, 0.12% Pacific Islander, and 6.81% from two or more races. Hispanic or Latino of any race were 47.4% of the population.[7]

There were 14,977 households out of which 33.3% had children under the age of 18 living with them, 38.5% were married couples living together, 20.1% had a female householder with no husband present, and 36.7% were non-families. 30.9% of all households were made up of individuals and 13.5% had someone living alone who was 65 years of age or older. The average household size was 2.57 and the average family size was 3.23.

In the city the population was spread out with 29.5% under the age of 18, 9.0% from 18 to 24, 26.8% from 25 to 44, 19.2% from 45 to 64, and 15.6% who were 65 years of age or older. The median age was 34 years. For every 100 females there were 88.1 males. For every 100 females age 18 and over, there were 81.3 males.

The median income for a household in the city was $ $33,242, and the median income for a family was $39,130. Males had a median income of $35,849 versus $26,652 for females. The per capita income for the city was $16,913. About 22.6% of families and 26.4% of the population were below the poverty line, including 41.7% of those under age 18 and 13.2% of those age 65 or over.

Politically, the city of Holyoke has recently supported candidates from the Democratic Party by a wide margin. In the 2012 elections, voters supported President Barack Obama over Mitt Romney by a margin of 76%-22%,[8] and Elizabeth Warren over incumbent Senator Scott Brown 70%-30%.[9] Holyoke elected an openly gay mayor, Alex Morse, in the 2011 municipal election.[10]

According to the 2003 FBI Report of Offenses Known to Law Enforcement Holyoke's crime rate in most categories was above the national average, in some categories, significantly. Most of these crimes are placed in the category of property theft, with a property crime count of 2,822.[11]

The retail sector has been a major employer since the construction of the Holyoke Mall, one of the largest shopping malls in New England, in 1979. Retail has provided the city with a large and steady tax base, contributing over $7 million in taxes annually.[13]

Historically, a city of working-class immigrants (and the business owners who employed them), the first wave of mill workers was predominantly Irish. Irish immigrants had begun to settle in the region before the construction of the dam and the industrialization that followed, which is why the area's early name was "Ireland's Parish." The Irish roots of Holyoke is still seen in its annual St. Patrick's Day Parade (see below).

In the 1850s, the mill owners began to recruit French-Canadians, who were viewed as more docile and less likely to form labor unions.[14] Later waves of immigration led to significant growth and cultural influence of communities of Germans, Poles, and Jews over first half of the 20th century. Starting in the 1950s, a large influx of Puerto Ricans and people from other Latino groups began to immigrate and migrate to Holyoke. Today Latinos form the largest minority group in the city, with the largest percentage Puerto Rican population of any city in the US outside Puerto Rico proper, at 44.7%.[15] The entire Latino population of Holyoke, as of the 2010 census, was 19,313, or 48.4% of the city's population of 39,880.

Holyoke is home to the second-largest St. Patrick's Day parade in the United States, surpassed only by the New York City parade.[16] Held annually since 1952 on the Sunday following St. Patrick's Day, the parade draws hundreds of thousands of people from across New England and the Eastern seaboard of United States. The Holyoke Saint Patrick's Day Parade typically attracts 350,000 to 450,000 people each year, although in certain years in the 1960s and 1970s when the March weather was "perfect", that number blossomed to what the police department estimated were 1,000,000 celebrants.[17]

The Puerto Rican community of Holyoke holds an annual Puerto Rican Day parade on the third weekend of July as part of an Annual Hispanic Family Festival held by La Familia Hispana, inc. Every year the parade grows in popularity, attracting Puerto Ricans from across the northeast.

Mayor Alex B. Morse, who first became an activist for LGBT rights as a high school student in Holyoke only six years earlier, presided at the city's first rainbow flag-raising ceremony in recognition of Gay Pride Month in June 2012.[18]

On February 9, 1895, William G. Morgan invented volleyball at the former Holyoke YMCA. That YMCA building was on High Street at the intersection with Appleton Street but has since been demolished. The Volleyball Hall of Fame resides in Holyoke at Heritage State Park and inducts a new class of athletes, coaches, and contributors every October. The sport was originally known as mintonette.

Holyoke School Department serves the city. Holyoke High School, William J. Dean Technical-Vocational High School, and the Paulo Friere Social Justice High School are the city's high schools. Holyoke Community College serves Holyoke and the western Massachusetts area. Holyoke Catholic High School was in Holyoke for five decades but is now in Chicopee.[20]

Holyoke Public Library, found at 335 Maple Street, is one of the very few examples of neoclassical architecture in the city of Holyoke. It sits on Library Park, which was donated by the Holyoke Water Power Company in 1887. In 1870 the library was originally in a room in the old Appleton Street School. In 1876 it moved to a large central room on the main floor of City Hall. It remained there until it was determined that it had outgrown the space and a modern facility was required.[21] Holyoke's citizens were charged to raise money to construct the library building and provide additional books. Under the leadership of Henry Chase, $95,000 was raised. William Whiting and William Skinner, each gave $10,000. Joseph Clough, the architect in charge of designing the building, gave his services gratis because his daughter was a faithful patron of the library. It opened officially in 1902.[22]

At the dedication ceremony William Whiting, who was library president at the time, referred to the library as the "people's college" and added that: “A library is as much a part of the intellectual life of a community as its schools, and should be supported generously as part of our educational system. Within these walls you will find authors devoted to literature, arts and science, and they are free to any who will ask. We can say to the citizens of Holyoke you have only to ask her and you will find knowledge to make your life useful and happy.”[21]

Raymond Kennedy (1934–2008), novelist, who set many of his books in a fictionalized Holyoke that he called "Ireland Parish" and "Hadley Falls".

Mike LaPlante (born 1966), college basketball head coach, NBA scout and lawyer. Known internationally as an excellent recruiter with contacts with the Senegalese Basketball Federation and credited with bringing many players into the NBA from Africa and Europe.